Studies on the Constituents of Asclepiadaceae Plants. XXXIV. Chemistry of Sarcostin
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概要
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(a) Partial acetylation of sarcostin (1) gave two diacetates ; 3,12-O-acetate (4) and 3,20-di-O-acetate (3) in 3 : 1 ratio, besides 3-mono-O-acetate (5) and 3,12,20-tri-O-acetate (2). On the other hand, benzoylation of 5 with equimolar amount of benzoyl chloride gave its 20-O-benzoate (6). (b) Treatment of 1 with paraldehyde under acid catalytic conditions afforded 14,17-12,20-di-O-ethylidene-sarcostin (14). (c) The configuration at C-20 position of 1 is S on the basis of the X-ray analysis of 3-O-p-bromobenzoate (16). The o-nitrobenzoate (17) showed a negative Cotton effect contrary to the expectation from Nagai's data but the 14,17-O-ethylidene derivative (18) of 17 showed a positive Cotton effect. (d) The configuration of the C-20 carbinol derived from sodium borohydride reduction of the corresponding ketone is ascribable to the stereochemistry at C-17 of the ketone. The 20-O-o-nitrobenzoate (24) derived from the sodium borohydride reduction product of lineolon diacetate (25) shows a positive Cotton effect while the o-nitrobenzoate (26) from isolineolon diacetate (27) shows a negative effect.
- 社団法人日本薬学会の論文
- 1975-08-25
著者
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三橋 博
Faculty of Pharmaceutical Sciences, Hokkaido University
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林 紘司
Faculty of Pharmaceutical Sciences, Hokkaido University
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三橋 博
Research Institute For Biology & Chemistry Tsumura & Co.
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三橋 博
Faculty Of Pharmaceutical Sciences Hokkaido University
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林 紘司
Tsumura Central Research Laboratories Tsumura & Co.
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林 紘司
Faculty Of Pharmaceutical Sciences Hokkaido University
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